Hydrochloric Acid → 1-(4-Fluorophenyl)-1-hexanone

HRID 988867Notes

Reaction equation

HRID 988867 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([Mg]Br)[CH2:12][CH2:13][CH2:14][CH3:15].Cl>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3].O1CCCC1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:7])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 678794-Fluorobenzoyl chlorideHCID 178445865HCID 178445865, compound

Product 1

HCID 111831661-(4-Fluorophenyl)-1-hexanone

Reagents, catalysts & solvents 2

HCID 5483663Ferric acetylacetonateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

100 mL of tetrahydrofuran was placed into a four-neck round-bottom flask, then 7.92 g (0.05 mol) of 4-fluorobenzoyl chloride and 0.53 g (1.5 mmol) of tris(acetylacetone)iron (III) were added and stirred under a nitrogen atmosphere. To this solution pentylmagnesium bromide was added at a room temperature and stirred at a room temperature for 10 min. After completion of the reaction, this solution was acidified with dilute hydrochloric acid and the organic phase was extracted with diethyl ether. Further, the organic phase was neutralized with satd. sodium hydrogencarbonate solution and washed with satd. sodium chloride solution. The organic phase was dehydrated with anhydrous magnesium sulfate, then diethyl ether was evaporated by a rotary evaporator and dried by a vacuum pump to obtain crude FPHxO.

Workup

  1. stirringstirred at a room temperature for 10 min
  2. customAfter completion of the reaction
  3. extractionthe organic phase was extracted with diethyl ether
  4. washsodium hydrogencarbonate solution and washed with satd
  5. customdiethyl ether was evaporated by a rotary evaporator
  6. customdried by a vacuum pump
  7. customto obtain crude FPHxO

Sources & evidence

ORD record
ord-d4cdf826c79547caa836719aafe08e03
Source dataset
uspto-grants-2003_10
Patent number
US06635782B2

Reaction notes

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